Why You Should Quit Slim Fit (And How)

It’s been a decade and a half of the reign of slim fit. The Ludlow suit from J.Crew ascended to dominance after designers like Thom Browne showed it on the runway. Pleats were banished and the contours of a man’s bottom half were a selling point.

I don’t advocate following fashion trends. My ideal is a trend-proof wardrobe, and the closest you can get to that is by sticking to proportions and silhouettes that are flattering on your body, which is usually neither crazy slim nor wildly loose.

That said there’s something about slim tailored clothing that has bothered me for several years: there’s no ability for the cloth to drape. No drape means no drama, no expression, no character.

When I think of elegance, the people I imagine are wearing clothes that drape, flowing and moving uniquely according to the individual fabric’s qualities. Heck, even think about classical sculpture—the masters of sculpture chisel draping fabric, creating drama and movement.

In the real world, our clothes get to do the real thing that the masters tried so hard to capture in hard, un-malleable marble.

what ppl what ppl
over 30 under 30
think are think are
"dad pants" "dad pants" pic.twitter.com/Wp9IzjFT0T

— derek guy (@dieworkwear) February 12, 2023

I chuckled at Derek Guy’s recent meme post—as someone over 30, I relate to this all too well. So diligently have I spent my adulthood escaping the loose, baggy, triple-pleated Dockers of my 90s-and-early-2000s youth, that I didn’t realize that I’m a dad myself, meaning by default anything I wear will be considered dad-wear by my kids. If I step back far enough I’ve also come to grips with the fact that the cyclical nature of fashion has resulted in Gen Z’ers who have embraced the clothes I so loathed in elementary and middle school. We’ll know things have gone too far when wallet chains and JNCOs have reappeared.

How to quit slim fit

Let’s say you’re new to style, and all you’ve known is slim-fit. Where do you start when trying to allow some expressiveness back into your clothes, without throwing everything away?

Here are a few do’s and don’t’s to help you out:

1. Don’t assume looser fits mean that the basic rules of well-fitting tailored jackets are different. 
   • While you can definitely stand to have a drapier chest, a slightly extended shoulder, and a little extra length in the jacket, there will still be a point where a jacket looks too big on you. The telltale signs of bad fit are all still applicable: if the sleeves hang down past your wrist, they’re too long; if the armholes are halfway down your ribcage, they’re still too low; if the back of the jacket is so loose between your shoulder blades that it would allow two people to comfortably fit inside, it’s still too big. 
   • I touched on two of these aspects of jacket fit here.
     
2. Do give your jacket a bit more room in the chest, waist and length. 
   • In the history of tailored clothing, something called the “drape cut” made its debut in the 20th century and forever altered the course of history. Invented by British tailor Frederick Scholte, it became the pattern on which London House and Attolini in Naples began work to create their infamous lightweight, drapey and comfortable take on tailoring. The drape cut helps you out aesthetically by emphasizing the difference between your chest and waist. And even someone with a dad bod, like myself, can benefit from this. Instead of the slim-everywhere look, which can look like sausage casing even on the most fit guy in his 20s, a more drapey cut can make your torso look athletic.
3. Don’t let your pants hem sag to the ground.
   • One of the things that made 90s/early-2000s tailoring look so sloppy (and to be frank, still plagues the majority of men) is that their already-loose pants had inseams that were 2-3 inches too long, resulting in pants pooling around the ankles. As a friend of mine pointed out, since a suit is defined as a jacket and pants made from the same fabric, those oversized, sloppy silhouettes basically looked like pajamas.
   • A hem with no break on a more full-cut trouser is still a great look, and men going back decades have sought to have their tailors give them that perfect shivering break.
     
4. Do experiment with a slight break.
   • As I’ve written before, on most guys a no-break trouser is not super flattering. It tends to shorten your legs unless your stature is 6’2”+ and your inseam 32”+. A slight break, particularly on moderately tapered trousers (that is, about 8” across measured flat), just visually makes your legs look longer, making you look taller and your legs look leaner.
     
5. Do wear higher-rise trousers.
   • Clothes should flatter your body. Higher rise trousers, proportional for your build, do that. The idea is that they make your legs look longer. It’s a no-brainer, and whatever mental hangups you have about high-rise trousers, you should put on hold and just give them a try. Many of the high rise pants are also going to have a pleat these days as well. Trust me, I understand your hesitation. But the point of the pleat is both utilitarian and aesthetic—it’s a little extra fabric that makes it more comfortable to sit down, and it elongates the front crease in your trouser all the way to the waistband, accentuating that length. Keep an open mind.
     

Start out by getting a tailored jacket from a brand that makes more classic tailoring, as opposed to the skinny-fit stuff that’s everywhere mainstream. I’ve built an archive of reviews about somewhat-niche-but-excellent-makers who each create tailored clothes that have a much more classic silhouette, with moderate or somewhat wider lapels, longer jacket lengths and a bit of room in the chest, plus trousers with medium or higher rises and somewhat wider legs. 

My favorite trousers come from Spier & Mackay—they use excellent fabrics, but are sold at a price point that’s hard to beat. Their contemporary fit is their wider fit, and they make some of their nicest trousers in a high-rise, single pleated model. Even their contemporary fit is pretty fitted by historical standards, but a size up with some alterations to the waist and seat would get you there. I take my normal size and like it just fine.

For jackets, within the classic-tailoring lines that exist, there’s a range of styles to experiment with to discover what’s flattering on you. Cavour makes a very Neapolitan-style jacket with narrower shoulders; Ring Jacket makes one with more extended shoulders. Anglo-Italian makes theirs in Naples, with an English twist in fabric palette; Besnard makes theirs in Northern Italy with a Florentine inspiration. They’re all fantastic.

I hope your journey to an expressive, beautiful, long-lasting wardrobe of clothes that make you look great, feel great, and express your style, is a productive one. If you need any help, feel free to reach out for advice!